I have a couple....
I signed Mark Trumbo to my expansion team originally as a stopgap at 1b/DH and he turned out to be a good player, averaging 28 homers and 90 RBIs in his three seasons with me. I was still rebuilding and traded him (and some backup catcher) to the Rockies for 4 prospects, including two of the top 15 pitching prospects in baseball. One of those guys made the jump from Double-A to the majors and he went down throwing his first pitch in his first start for 11 months. The other pitcher made two starts at Double-A and in his third, he was injured and was out 8-9 months.Neither guy ever lived up to their potential and both were gone over the next two seasons.
In another league I did the opposite, I mortgaged the farm (gave up my top 6 prospects) to acquire a top starting pitcher and outfielder to make a run at the World Series. The outfielder was hurt running to third in his 4th game with me and missed the rest of the season with an ankle injury, and the starting pitcher went down in his 3rd start and ended up retiring at the end of the season. Needless to say, I was relieved of my GM duties two years later after two 90+ loss seasons and a minor league system ranked 29th.
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